Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment

Abdelrahim，Mohamed1; Zhang，Jun2,4; Gao，Quan1; Zordok，Wael A.3; Liu，Ji2; Geng，Jin1

2022

10.1021/acsapm.2c01357

ACS Applied Polymer Materials   Impact Factor & Quartile

2637-6105

2637-6105

Thermosets are rigid, infusible, and unmolded materials containing three-dimensional (3D) cross-linked structures. They are considered a fundamental pillar in the international economy, which are produced by 65 million tons annually. The responsive cross-linking moieties provide the thermosets characterized with outstanding physicochemical properties such as stiffness, degradability, and chemical and thermal resistance. We prepared degradable thermoset materials using thioketal (TK) cross-linkers, which underwent main-chain or side change degradation in the presence of hydrogen peroxide in water. TK cross-linkers at different concentrations (5, 10, and 20% wt %) were polymerized with 2-hydroxyethyl acrylate (HEA) or with 2-hydroxyethyl methacrylate (HEMA) and 1-vinyl-2-pyrrolidone (PD) to produce cross-linked poly(HEA) and poly(HEMA-PD) by free radical polymerization, respectively. The resultant polymer materials completely degraded in hydrogen peroxide/water (3-30%, vol). Using isophorone diisocyanate, we also produced degradable polyurethane based on TK-bearing diol. We prepared a 3D degradable thermoset using the Direct-Ink-Writing (DIW) 3D printing technology, which was charged by diethylene glycol diacrylate (15%, wt %) and a prepolymer (isophorone diisocyanate terminated by acrylate moieties) containing diol-thioketal linkage (15%, wt %). Finally, we found that TK-poly(HEA) underwent microbial degradation by Lactobacillus jensenii at 37 °C, which indicates a benign eco-friendly effect.

biodegradation hydrogen peroxide polyurethane thermosets thioketal

SCI

English

Corresponding

National Natural Science Foundation of China[22071263] ; Natural Science Foundation of Guangdong Province, China[2020A1515010994] ; Guangdong Province Zhujiang Talents Program[2019QN01Y127] ; Shenzhen Fundamental Research Program[JCYJ20200109110215774]

Materials Science ; Polymer Science

Materials Science, Multidisciplinary ; Polymer Science

WOS:000869694900001

AMER CHEMICAL SOC

2-s2.0-85139723647

Scopus

1.Shenzhen Institute of Advanced Technology,Chinese Academy of Sciences,Shenzhen,518055,China
2.Department of Mechanical and Energy Engineering,Southern University of Science and Technology,Shenzhen,518055,China
3.Department of Chemistry,Faculty of Science,Zagazig University,Zagazig,44519,Egypt
4.Research and Innovation Center,SKG Health Technology,Shenzhen,518063,China

Abdelrahim，Mohamed,Zhang，Jun,Gao，Quan,et al. Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment[J]. ACS Applied Polymer Materials,2022.

Abdelrahim，Mohamed,Zhang，Jun,Gao，Quan,Zordok，Wael A.,Liu，Ji,&Geng，Jin.(2022).Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment.ACS Applied Polymer Materials.

Abdelrahim，Mohamed,et al."Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment".ACS Applied Polymer Materials (2022).